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MS has Hotmail problem?!

Been troubleshooting my mail servers for several days, thinking something is messed up on my servers, not being able to send emails to hotmail accounts...
After lots of troubleshooting, by myself and some help from here, specially from zENGER, I decided to contact Microsoft.

It turns out to look like they actually have something messed up on their end. The support people I've been talking to so far has been really lame, and it feels like I have to teach them what to look for, and why it's not working correctly.

So now I'm posting here in hope of finding the REAL SMTP gurus to help me out...heh?!

My conclusions so far are these:
1. Telnet to mx3.hotmail.com 25(one of the mx mail server records) hardly ever works.. actuall it has worked ONCE out of maybe 100 tests.. heh! The funny part making the telnet session is you get a 250 (OKAY) response from their mailserver, accepting it for delivery!
2. Sending an email from same computers as I've been trying to telnet from, via Exchange or Groupwise DOES work!
3. Since MS told me telnet should work, I believe they must have installed some new spam device or something along that line, that they have not configured right, causing emails to just disappear.
4. The light version of MS SMTP service that comes by default with Win2000 Server does NOT work.

Hopefully you know a lot more about this stuff than me, and can tell if something really seems to be wrong from your end too, or if everything is fine from your end!?

I feel like I'm not sufficient, in convincing MS they have something wrong with their email system.

They are trying to tell me it must be something wrong with my system, either firewall, virus/spam filter, or routers...

Well, I have tried from several different computers, including from my Charter cable at home, all with the same result... their mx3.hotmail.com mail server accepts the message and queues it for delivery, and still it doesn't reach the recipient.

Here is a telnet example log from my home: (X'ed out all personal info)

Unless I don't understand it completely right, to me this looks like it can't have anything to do with me, the email was left in "their hands" when it got 'Queued mail for delivery' by their mx3.hotmail.com mail server. It shouldn't have anything to do with any of my computer/software/network after that point?!

Both yesterday and today I have sent and forwarded messages to my hotmail account...and received them...and my kids hotmail accounts...not sure about todays yet...but they got yesterdays emails...this is muliple accounts...and they all work?

So...maybe there is some spelling error? in the address?

MLF

How people treat you is their karma- how you react is yours-Wayne Dyer

Originally posted here by morganlefay So...maybe there is some spelling error? in the address?

MLF

No, I've been very careful, and kept logs, as you can see in my previous message, so I can see afterwards there are no spelling errors...

If you can send emails from your email clients, like Outlook, Outlook Express, Groupwise without any problems, then that is what we can do too.
BUT, if you use special application servers that are sending outgoing emails via the SMTP service included on Win2000 Server, or if you try to simulate same thing with a telnet session, just like in my example in previous message, then it doesn't work, even though their hotmail server seems to accept it...

220 mc11-f17.hotmail.com Sending unsolicited commercial or bulk e-mail to Micros
oft's computer network is prohibited. Other restrictions are found at http://pri
vacy.msn.com/Anti-spam/. Violations will result in use of equipment located in C
alifornia and other states.

This is simply a connection banner.

Now, looking at the ESMTP codes (250, 354, etc.), it appears that the system accepted your manual input and queued the mail.

Moreover, when I try this, the host immediately closes the connection on me when I try to telnet to it.

Our scars have the power to remind us that our past was real. -- Hannibal Lecter.
Talent is God given. Be humble. Fame is man-given. Be grateful. Conceit is self-given. Be careful. -- John Wooden

1. Not sure yet how MS defines a "too short" email, but obviously if you do test emails via telnet it's real easy to get filtered out. Kills the message without even notifcation to sender or recipient, even if the recipient has your domain on the "trusted" list.

2. Norton's "E-maill Protection" listens on port 25 for any communication. Every time an email is going out on port 25, Norton intercepts it, and Hotmail will reject it.. heh!! Funny thing is most other email addresses are fine, only Hotmail having an issue with Norton. Requested MS to work out the problem with Symantec, and they said they were going to try to find a solution right away!

I'm pretty amazed there is not more about this problem around on the internet. I guess one possibility is that nobody knows they are having this issue.. heh!??!

Guess there are not a whole lot of people here on AO who knows a whole lot about how SMTP works. But if you are interested in testing any of this any further, or want to check if you are having any problems sending emails from your company as well, let me know, and I will gladly provide as much info as I can.

I think the more likely solution is that very few people who know about SMTP rely on free email services such as hotmail for their automated mailings. MS isn't going to spend much time on it because you don't pay them that much for the service, ie. nothing.

For item #2- most new AV products listen on port 25 and stop all outgoing emails. You can usually shut that off in the options for you AV. I know that McAfee 8.0i automatically stops all outbound port25 traffic.